I don’t think there is an easy way to DeDRM the latest kindle format used by the Mac/pc and iOS reader, and there is no easy way to download all kindle books in your account for “transfer to device via usb” for e-ink devices all at once. I’m trying to archive my 4k or so kindle books (already did a similar number of audible using openaudible) because I don’t trust Amazon to preserve access to them indefinitely.
Anecdotally, I've become aware that the Windows Kindle installer version 1.17 works fine for downloading your paid-for Kindle books and format-shifting them or making a personal back-up in a more open form. That information was current about a year or so ago; hopefully that version has not been hobbled since. Also, disable auto-updating.
I strongly suggest you only use it for your own purchases. Authors need to heat and eat too.
Kindle 1.26 works as of a week ago, if you also install the KFX Input in addition to dedrm. Best to look at the readme for such tools to get the latest info in any case.
I’m away from my M1 Mac at the moment so I’m not sure which older version of Kindle I ended up installing, but it worked fine to download my books, which was all I needed it to do.
This is indeed how I have read books, recently. I installed an old Kindle app on the PC, and configured it with my Amazon account. I download the books through the app, then start Calibre with the deDRM plugin which will find my private key directly in the Kindle directory, and convert the books to epub. I then send them to my Kobo reader via USB.
The problem is that the latest versions of the Amazon reader for PC and Mac don't download the books in a format compatible with Calibre's DeDRM scripts. This is compounded by Amazon flipping off the choice to always update the software automatically (yes, it's stated as "always update automatically" if checked), so the first thing you have to do when starting up is go into settings and make sure the checkbox is cleared.